Westchester, NY Homes

/27
$210,000
- 2 Beds
- 1 Bath
- 672 Sq Ft
135 - 6 Highland Ave S Unit D1, Ossining, NY 10562

Discover this charming, updated two-bedroom co-op in highly sought-after Highland Terrace. This unique unit offers the convenience of both a main building entrance and its own private entry. Inside, you'll find a spacious and bright primary bedroom with ample closet space, while the versatile second bedroom That is currently being utilized as a home office. Abundant windows fill the living areas

Sherry Wiggs

Houlihan Lawrence Inc.

(914) 601-2993

135 - 6 Highland Ave S Unit D1, Ossining, NY 10562
Explore New Castle Township
/12
$9,400 per month
- 4 Beds
- 3.5 Baths
- 2,468 Sq Ft
- House for Rent
187 Croton Ave, Mount Kisco, NY 10549

Move right in to this bright and sunny recently renovated 4 bedroom home in the Chappaqua School District. Enjoy easy living and a great layout for entertaining family and friends. Open concept kitchen - family room with access to wrap around deck and great yard. 1st floor primary with renovated en-suite, walk in closet and sliders to deck, living room, dining room and powder room complete the

Deena Bouchier

Compass Greater NY, LLC

(914) 814-6734

187 Croton Ave, Mount Kisco, NY 10549
$1,623,500 Sold Aug 14, 2025
- 2,539 Sq Ft
- $639/SF
- 14 Days On Market
- 4 Beds
- 2.5 Baths
- Built 1973
24 Glen Terrace, Chappaqua, NY 10514

Welcome to 24 Glen Terrace, Chappaqua, a gracious and well-maintained Colonial imbued with country charm serenely set at the end of a quiet cul-de-sac. Welcoming tiled entry foyer introduces expansive front-to-back living room with double French doors, large front-facing bay window and slider to rear deck. Adjoining formal dining room with fireplace easily accommodates feasts or fests. A skylit,

Stacy Levey William Raveis-New York, LLC

24 Glen Terrace, Chappaqua, NY 10514

Est $920,596 Not Listed For Sale
- 4 Beds
- 3 Baths
- 2,688 Sq Ft
16 Seth Canyon Dr, Mount Kisco, NY 10549

16 Seth Canyon Dr, Mount Kisco, NY 10549

/35
$1,350,000 Pending
- 6 Beds
- 4 Baths
- 5,034 Sq Ft
62 Taconic Rd, Millwood, NY 10546

MOTIVATED SELLER! PRICE REDUCED! Welcome to this spacious, peaceful, and impeccably maintained 6-bedroom, 4-bathroom home with tennis court and pool in the highly sought-after Chappaqua School District (Millwood). This home offers 5,034 sq ft of move-in ready living space on a scenic and private 2-acre lot. The large rooms and easy layout provide the perfect canvas to create your dream home

Hillary Landau

Compass Greater NY, LLC

(914) 996-2889

62 Taconic Rd, Millwood, NY 10546
/25

$2,400 - $6,850 per month

Chappaqua Crossing Apartments

1 - 3 Beds

480 Bedford Rd, Chappaqua, NY 10514

Wilder Balter Partners, Inc., Hudson valley's premier developer of luxury homes has written a new chapter for the iconic reader's digest building. The four-story structure has undergone an unprecedented renovation, and the finished product embraces the nostalgia of the old media empire's headquarters with the extravagance of contemporary housing. Chappaqua Crossing Apts is now open! Please call

480 Bedford Rd, Chappaqua, NY 10514
$1,172,018 Sold Aug 13, 2025
- 2,334 Sq Ft
- $502/SF
- 7 Days On Market
- 4 Beds
- 2.5 Baths
- Built 1947
180 Millwood Rd, Chappaqua, NY 10514

Welcome to a home full of warmth, charm, and everyday comfort — perfectly situated right across from beautiful Gedney Park and just around the corner from the elementary school.This inviting 4-bedroom, 2.5-bathroom home has everything you need for easy, relaxed living. Step inside to a bright and welcoming living room, a private office ideal for working from home, and a comfortable family

Danae Richards William Raveis-New York, LLC

180 Millwood Rd, Chappaqua, NY 10514

Est $666,647 Not Listed For Sale
- 2 Beds
- 2.5 Baths
- 1,918 Sq Ft
36 Ledgewood Commons, Millwood, NY 10546

36 Ledgewood Commons, Millwood, NY 10546

/49
$2,200,000
- 5 Beds
- 4.5 Baths
- 4,172 Sq Ft
77 Haights Cross Rd, Chappaqua, NY 10514

Timeless elegance meets modern comfort in this enchanting 1901 hunting lodge, masterfully restored in 1991 and recently enhanced. Set on beautifully landscaped grounds with lush gardens, this distinguished home features a dramatic front portico, high ceilings, intricate millwork, and unique architectural details throughout. Grand living spaces include a library/home office with French doors and

Joshua Rogull Julia B Fee Sothebys Int. Rlty

77 Haights Cross Rd, Chappaqua, NY 10514
/13
$6,850 per month
- 3 Beds
- 2.5 Baths
- 2,200 Sq Ft
- Apartment for Rent
480 Bedford Rd Unit 401, Chappaqua, NY 10514

Stunning 3 Bedroom, 2.5 baths with loft apartment the Chappaqua Crossing Community. Two landscaped interior courtyards. On-site walking trail. Resident superintendent and on-site property management. Outdoor playground area, Large gym and separate exercise room, Two laundry rooms, Beautiful club/multi-purpose room, including kitchenette. Elegant reading library with dramatic views. The

Donna Lee Blais Northridge Realty

480 Bedford Rd Unit 401, Chappaqua, NY 10514
$2,282,000 Sold Aug 11, 2025
- 5,254 Sq Ft
- $434/SF
- 17 Days On Market
- 4 Beds
- 6 Baths
- Built 1990
92 Random Farms Dr, Chappaqua, NY 10514

Welcome to 92 Random Farms Drive, ideally located in the sought-after Random Farms community of Chappaqua. Completely renovated in 2022, this stunning turnkey residence showcases modern design, luxurious upgrades, and an open layout tailored to today’s lifestyle.The main level features a dramatic double-height entry foyer, a gourmet kitchen outfitted with premium appliances, a sunlit living

Sari Shaw Compass Greater NY, LLC

92 Random Farms Dr, Chappaqua, NY 10514

Not Listed For Sale
- 4 Beds
767 King St, Chappaqua, NY 10514

767 King St, Chappaqua, NY 10514

/44
$1,774,000
- 3 Beds
- 3.5 Baths
- 3,614 Sq Ft
21 Wallace Way, Chappaqua, NY 10514

Better than new at Chappaqua Crossings Carriages! Be among the first to experience this spectacular new community featuring a delightful and charming village atmosphere in the heart of Westchester, Chappaqua, NY. This stunning “Byram Newhaven model” situated in a prime location within the community, offers great curb appeal with its expansive front porch, stone walls and specimen plantings; and

Ken Wile Redfin Real Estate

21 Wallace Way, Chappaqua, NY 10514
/32
$5,600 per month
- 2 Beds
- 2.5 Baths
- 1,495 Sq Ft
- Townhouse for Rent
44 Brook Farm Close Unit 44, Chappaqua, NY 10514

Old Farm Lake Condo complex - Recent renovation includes new porcelain tiled entry and Kitchen floors, new white eat-in kitchen with quartz counters. range, refrigerator and DW. This 2 Bedroom unit has been freshly painted, new lighting fixtures, Washer & Dryer on second floor, each bedroom has a full bath, wood floors throughout and new windows, Primary BR has a large walk-in closet, Enter

Janet Auer Coldwell Banker Realty

44 Brook Farm Close Unit 44, Chappaqua, NY 10514
$1,825,000 Sold Aug 11, 2025
- 3,814 Sq Ft
- $479/SF
- 7 Days On Market
- 3 Beds
- 3.5 Baths
- Built 1956
33 W Orchard Rd, Chappaqua, NY 10514

Beautiful, spacious, completely renovated three bedroom, four bathroom ranch style home that lives like a five bedroom on a quiet cul-de-sac neighborhood street in the Chappaqua school district. This home has undergone a comprehensive renovation in the last 8 years where every detail has been carefully crafted to blend sophistication, elegance, and functionality. The rear private yard

Amanda Goldberg William Raveis-New York, LLC

33 W Orchard Rd, Chappaqua, NY 10514

Not Listed For Sale
- 4 Beds
- 3.5 Baths
- 4,477 Sq Ft
38 Taylor Rd, Mount Kisco, NY 10549

38 Taylor Rd, Mount Kisco, NY 10549

/9
$1,807,995 Pending
- 2 Beds
- 3.5 Baths
- 3,269 Sq Ft
2 Carriage Ln Unit 81, Chappaqua, NY 10514

HOME IS TO BE BUILT. 2 BR very popular Greeley Floorplan with primary on first floor. We have a model of this home to walk through. It is ideally sized at 3,269 sq. ft. and includes 2 BR + office, huge loft, finished basement with media room and full bath. The 2-story open concept great room and kitchen allow for large family gatherings. The open island with ample seating beckons your inner

Thomas Jacovino Toll Brothers Real Estate Inc.

2 Carriage Ln Unit 81, Chappaqua, NY 10514
/11
$3,700 per month
- 1 Bed
- 2 Baths
- 884 Sq Ft
- Apartment for Rent
91 Bedford Rd Unit 3, Chappaqua, NY 10514

LIVES LIKE A TWO-BEDROOM. Master bed/bath, Den/bed. High Ceilings. Quality construction by highly regarded local builder. Glamorous modern styling: quartz counters, bright open floor plans, LED lighting, + individual balcony, storage closet. HW/heater & W/D. Amenities of this architecturally inspired bldg include Access control intercom/security cameras., FOB. Steel & concrete frame, rock wool

Grace Priore ERA Insite Realty Services

91 Bedford Rd Unit 3, Chappaqua, NY 10514
$1,090,000 Sold Aug 08, 2025
- 1,874 Sq Ft
- $582/SF
- 34 Days On Market
- 4 Beds
- 2 Baths
- Built 1955
83 Inningwood Rd, Millwood, NY 10546

Newly staged and a pleasure to show! Perched gracefully on a hill, this striking mid-century modern home is a testament to architect Aaron Resnick’s creative vision, shaped under the mentorship of Frank Lloyd Wright. Embracing the philosophy that architecture should harmonize with its surroundings, the design flows seamlessly with the natural topography rather than imposing upon it.With all

Amy Via Houlihan Lawrence Inc.

83 Inningwood Rd, Millwood, NY 10546

Not Listed For Sale
- 4 Beds
- 3.5 Baths
- 2,280 Sq Ft
9 McKesson Hill Rd, Chappaqua, NY 10514

9 McKesson Hill Rd, Chappaqua, NY 10514

/39
$1,399,000
- 3 Beds
- 2.5 Baths
- 2,830 Sq Ft
27 Deepwood Hill, Chappaqua, NY 10514

Hywood Ledge is a spectacular expanded ranch in the desirable Deepwood neighborhood of Chappaqua, which presents sophisticated charm and tranquility. This cedar-shake beauty is perfectly situated at the end of a cul-de-sac on 1.9 acres, offering unparalleled privacy, yet only 5 minutes to the center of town and the Chappaqua Metro-North. The home was renovated between 2000-22 offering years of

Brendan Preston Houlihan Lawrence Inc.

27 Deepwood Hill, Chappaqua, NY 10514
/12
$4,500 per month
- 2 Beds
- 2.5 Baths
- 1,408 Sq Ft
- Townhouse for Rent
82 Pheasant Run Unit 82B, Millwood, NY 10546

Welcome to this beautifully updated 2-bedroom, 2.5-bath condo in the desirable Pheasant Run community. Located in the Chappaqua School District, this home offers the perfect blend of comfort, convenience, and lifestyle.The main level offers a welcoming layout with an eat-in kitchen that opens to the spacious living and dining area—ideal for entertaining. Enjoy cozy evenings by the

Jill Urban Compass Greater NY, LLC

82 Pheasant Run Unit 82B, Millwood, NY 10546
$1,890,000 Sold Aug 08, 2025
- 4,561 Sq Ft
- $414/SF
- 7 Days On Market
- 5 Beds
- 3.5 Baths
- Built 1785
42 Seven Bridges Rd, Chappaqua, NY 10514

Featured in Westchester magazine’s “Best Places to Live 2016” as an outstanding example of a Federal style colonial residence, this one-of-a-kind classic offers architectural integrity combined w impeccable present day renovations & amenities. This 5BR/3.1Bth colonial offers center hall layout, multiple fireplaces, exposed hand hewn beamed ceilings, post & beam construction in upper level, wide

Sena Baron William Raveis-New York, LLC

42 Seven Bridges Rd, Chappaqua, NY 10514

Not Listed For Sale
- 4 Beds
- 3.5 Baths
- 3,427 Sq Ft
16 Maria Ln, Ossining, NY 10562

16 Maria Ln, Ossining, NY 10562

/35
$2,195,000
- 4 Beds
- 3.5 Baths
- 4,004 Sq Ft
4 Circle Dr, Mount Kisco, NY 10549

Brand New Construction in the award-winning Chappaqua School District set on over one level acre. Ready for occupancy at the end of July or early August 2025 – just in time for the new school year. With 4 bedrooms and 3.1 bathrooms, it offers a flexible and functional layout with spacious, sunlit interiors that feel welcoming and refined. The open-concept living and dining areas are complemented

Aurora Banaszek Compass Greater NY, LLC

4 Circle Dr, Mount Kisco, NY 10549
/21
$6,250 per month
- 3 Beds
- 2 Baths
- 1,912 Sq Ft
- House for Rent
235 Douglas Rd, Chappaqua, NY 10514

This beautifully updated rental offers a bright, open layout and a prime location just under a mile from downtown Chappaqua and the Metro North station—perfect for easy commuting and enjoying all the local spots. Freshly painted and move-in ready, the home is available furnished or unfurnished.The main level features a sun-filled living and dining area, an updated kitchen, a spacious

Danielle Della Pella Compass Greater NY, LLC

235 Douglas Rd, Chappaqua, NY 10514
$1,325,000 Sold Aug 07, 2025
- 2,665 Sq Ft
- $497/SF
- 27 Days On Market
- 4 Beds
- 2.5 Baths
- Built 1972
51 Hidden Hollow Ln, Millwood, NY 10546

How about a picture-perfect, 4 bedroom, 2 1/2 bath colonial privately nestled behind a small stand of trees and offering a backyard paradise? Plus, it’s move-in ready. From the moment you turn down the spacious driveway, step out of your car, and walk up to the porticoed front entrance, you will have a lot to look forward to upon stepping inside. Open the front door and you’ll find yourself

Mary Case Friedner Corcoran Legends Realty

51 Hidden Hollow Ln, Millwood, NY 10546

Not Listed For Sale
- 6 Beds
- 5 Baths
- 3,853 Sq Ft
229 Pinesbridge Rd, Ossining, NY 10562

229 Pinesbridge Rd, Ossining, NY 10562

/16
$1,450,000
- 4 Beds
- 5 Baths
- 2,875 Sq Ft
136 Roaring Brook Rd, Chappaqua, NY 10514

Experience the pinnacle of refined living in this newly reimagined modern farmhouse, perfectly sited on a secluded, tree-lined acre in the heart of Chappaqua. With over 2,800 square feet of exquisitely finished space, this residence blends timeless architectural detail with sophisticated, high-end design for the ultimate in quiet luxury. Andersen 400 series windows and doors throughout, most are

Aric Wiser Douglas Elliman Real Estate

136 Roaring Brook Rd, Chappaqua, NY 10514
/34
$9,000 per month
- 4 Beds
- 3 Baths
- 3,009 Sq Ft
- House for Rent
200 Millwood Rd, Chappaqua, NY 10514

Tucked away in a 3+ acre private storybook setting, this reimagined farmhouse blends timeless charm with modern comfort. Set back from the road on a scenic, private property with gorgeous mature landscaping, two tranquil ponds, and wide-open views, this 4-bedroom home is a peaceful retreat unlike any other.Inside, the open, sunlit layout features oversized windows that invite the outdoors in,

Sari Shaw Compass Greater NY, LLC

200 Millwood Rd, Chappaqua, NY 10514
$1,445,000 Sold Aug 07, 2025
- 2,652 Sq Ft
- $545/SF
- 5 Days On Market
- 3 Beds
- 3 Baths
- Built 1951
12 Pond Hill Rd, Chappaqua, NY 10514

Picture perfect Cape on level landscaped property with lush lawns radiates curb appeal. Beautifully updated and impeccably maintained with a blend of classic charm and modern luxury. Light-filled rooms with gleaming hardwood floors enhance the well proportioned living spaces. The renovated eat-in kitchen features white cabinetry, stainless steel appliances, quartz countertops and tasteful

Jennifer Harris Compass Greater NY, LLC

12 Pond Hill Rd, Chappaqua, NY 10514

Not Listed For Sale
- 8 Beds
- 8 Baths
- 5,337 Sq Ft
51 Pinesbridge Rd, Ossining, NY 10562

51 Pinesbridge Rd, Ossining, NY 10562

/36
$1,795,000
- 4 Beds
- 3.5 Baths
- 4,576 Sq Ft
20 Little Pine Rd, Mount Kisco, NY 10549

Located at the end of a quiet cul-de-sac, 20 Little Pine Road is a Modern Farmhouse Colonial situated on over an acre of beautifully landscaped grounds. Interior spaces are light and fresh with a wonderful floorplan for everyday living. Approximately 4600 square feet, it houses nine main rooms on two levels. There is additional finished living space in the walk-out lower level. Interior spaces

Mary Dowdle Ginnel Real Estate

20 Little Pine Rd, Mount Kisco, NY 10549
/24
$9,750 per month
- 4 Beds
- 3.5 Baths
- 3,882 Sq Ft
- House for Rent
777 Armonk Rd, Mount Kisco, NY 10549

Set on over five secluded acres with picturesque pond and woodland views, this beautifully furnished 4-bedroom home offers a perfect blend of timeless character and modern comfort. Ideal for short- or long-term stays, the residence is thoughtfully designed for both relaxation and functionality.The main level welcomes you with a gracious entry foyer, a chef’s kitchen with premium

Mark Sanford Berkshire Hathaway HS NE Prop.

777 Armonk Rd, Mount Kisco, NY 10549
$1,560,000 Sold Aug 07, 2025
- 2,246 Sq Ft
- $695/SF
- 10 Days On Market
- 3 Beds
- 2.5 Baths
- Built 1935
45 Crossways, Chappaqua, NY 10514

Storybook 1930’s-era Tudor-style shingle cottage delightfully renovated & updated with all the comforts for the 21st century. Believed to be originally derived from Standard Homes Co. classic Densmore model. A welcoming entry vestibule with French door introduces a wide, front-facing living room, warmed by a stout wood-burning fireplace. Gather together in the dining room to enjoy holiday feasts

Stacy Levey William Raveis-New York, LLC

45 Crossways, Chappaqua, NY 10514

Not Listed For Sale
- 4 Beds
- 3 Baths
- 2,644 Sq Ft
130 Pinesbridge Rd, Ossining, NY 10562

130 Pinesbridge Rd, Ossining, NY 10562

/43
$2,000,000
- 6 Beds
- 6 Baths
- 5,234 Sq Ft
50 Overlook Dr, Chappaqua, NY 10514

50 Overlook Drive, an elegant 6-bedroom colonial Tudor set in a quiet, tree-lined neighborhood. With fresh upgrades completed this month, including interior repainting, carpet-removal to expose wood floors. This one-of-a-kind home is a must see. Meticulously maintained heating and cooling systems, brick exterior, and a classic-tile roof are some of the exceptional features this home can

Wendy Nolan Houlihan Lawrence Inc.

50 Overlook Dr, Chappaqua, NY 10514
/29
$5,000 per month
- 4 Beds
- 2 Baths
- 1,900 Sq Ft
- House for Rent
49 Spring Valley Rd, Ossining, NY 10562

A rare rental opportunity for a totally renovated Vintage country estate set home. . 49 Spring Valley offers the perfect balance of peace and quiet in a location close to all the modern creature comforts you seek. Step inside the main house's freshly-painted entry hall and admire the gleaming hardwood flooring. The gourmet kitchen is the heart of the home, featuring granite counters, 42"

Maria Vele Keller Williams Realty Partner

49 Spring Valley Rd, Ossining, NY 10562
$875,000 Sold Aug 06, 2025
- 2,541 Sq Ft
- $344/SF
- 32 Days On Market
- 4 Beds
- 2.5 Baths
- Built 1964
341 Millwood Rd, Chappaqua, NY 10514

Nestled on nearly 2 acres of serene, wooded land, this beautifully maintained 4-bedroom, 2.5-bath home offers space, comfort, and privacy. The bright and airy eat-in kitchen features abundant cabinet space, a convenient in-kitchen laundry, and a large picture window overlooking the scenic backyard. A sun-filled living room with an oversized picture window enhances the home's warm and inviting

Jo Ann Reilly Julia B Fee Sothebys Int. Rlty

341 Millwood Rd, Chappaqua, NY 10514

Est $1,569,374 Not Listed For Sale
- 4 Beds
- 3.5 Baths
- 2,973 Sq Ft
370 Sarles St, Mount Kisco, NY 10549

370 Sarles St, Mount Kisco, NY 10549

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